Odd outlook issue
 

OK, we have Exchange 2010 and I have a user with Win 7/Outlook 2013 and when their connection changes it prompts them for the password. I thought it was a DNS issue but when Outlook doesn't want to connect they are not able to connect via OWA on the web either as it says invalid credentials. They also use an iPhone which works even when the other two methods do not. It does happen more often when they unplug the laptop and take across campus and it goes to sleep. Otherwise when changing from wired to wireless it stays connected to Exchange just fine. It happens more when they take the laptop home and boot from home, start the VPN and try to connect.

Any ideas?

Just call the IT department manager! ;)

The IT Director is no help at all, that's why he said ask around!

https://www.eclectablog.com/wp-conte...ot-so-good.png

I'd be looking at client side DNS settings, esp if the OWA does a redirect to one of your domains for authentication.

Outlook servers tend to redirect to invalid internal IP addresses as part of their default mail routes which causes all sorts of mayhem because they see themselves as a security risk.

Which, technically, I guess they should :D

Happy postfix+dovecot w/ mysql back end and virtual domains/users here ...

Make sure autodiscover is configured correctly both internally and externally.

in 2010 MS used web access for PC/Mac Outlook and OWA so dns server name is mucho importanté.
Phones use ActiveSync besides different ports active sync can be handled by different servers/IPs.

With more modern Outlook it now uses autodiscover to find where the server is located. That way it can be moved around for availability and server maintenance. So your DNS/IP address might be finding a server, but not one that is currently hosting your domain.

It looks like they are moving toward everything using active sync.

Until about 6 months ago my desktop would chime letting me know Outlook had received a new email. The in about 3-5 seconds my phone would ding letting me know the new message had arrived. Now it is much different. My phone dings, and then the message arrives 20 to 50 seconds later to my desktop Outlook.

We host internally and the autodiscover is correct and you can connect to OWA, which is on the Exchange server, internally or externally and all the other 300 employees have no issues. That is why I was thinking client DNS but if they can connect to our mail.conoco.com via OWA (but still says invalid credentials) it should be past a DNS issue. I also think it is odd they can switch to a different VLAN when they move across campus wirelessly but if it sleeps in between moving it has the issue. I looked through the hub transport settings and client access for both organization and server and it all looks correct.

Looks like I need to see what is going on in the client.

This was a MS shop when I got here, but we have really had few issues.

Ahha, moving to different VLan and Outlook getting lost if the machine goes to sleep but OWA works but won't login.
Ding ding ding...
Make sure the Vlans gots proper PORTs/etc routed. IE port 80 routes (a default), but not secure port for login!
Same difference with Outlook and it's Ports.

I will double check those but I would think others would be having issues as they walk around. Then again, I might boot that one machine from the domain controller and DHCP and bring it back.

First, I am going to go eat the IT guys lunch.

OWA typically requires an organizational unit either in the url string or can be preset in client prefs

Example

Pelicanparts.com/ot where ot is the organizational unit

Assuming you have more than one organizational unit

Yeah, the ou is correct, I was too lazy to type it all out. Sorry.

They are out of the office today so I will mess with it next week.

It might be just coincidence that the OWA and Outlook crapping out. I wonder if the stored credentials in the Account Settings is messed up, but we did rebuild that profile. If it is messed up though, it would lock the account and that would also kill OWA. Just thinking out loud.